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Things to do in Chicago

Things to do in Chicago

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 "Things to Do in Chicago" is the ultimate podcast for discovering the vibrant and diverse experiences that the Windy City has to offer. Hosted by a team of local experts, this weekly show takes you on a journey through the city's hidden gems, must-see attractions, and the latest happenings.

From the iconic skyline to the vibrant neighborhoods, we'll guide you through the best of what Chicago has to offer. Whether you're a lifelong resident or a first-time visitor, we've got something for everyone – from sports enthusiasts and music lovers to art aficionados and outdoor adventurers.

Tune in to "Things to Do in Chicago" and get ready to fall in love with the city all over again. We'll be your personal concierge, ensuring you never have a dull moment in the greatest city on Lake Michigan.


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    • Exploring Chicago's Vibrant Culture: Music, Art, Sports, and More

      Exploring Chicago's Vibrant Culture: Music, Art, Sports, and More
      Jun 21 2025
      Chicago, a city renowned for its vibrant culture, rich history, and diverse entertainment options, offers a plethora of activities that cater to all interests. For tourists and locals alike, here are some fun, entertaining, and unique things to do in this dynamic city.

      If you are in Chicago on June 21, 2025, you might want to check out the Winnetka Music Festival, which kicks off at 4:00 PM. This event promises a day of music, making it a great way to spend your afternoon. Alternatively, if you're a fan of rock music, Queens of the Stone Age will be performing at the Huntington Bank Pavilion at Northerly Island, providing an energetic and memorable night out.

      For art enthusiasts, Chicago has several exciting events. The 57th Street Art Fair, held on June 7-8, is a 78-year-old tradition that brings together over 150 artists in Hyde Park. Here, you can browse and purchase artwork, enjoy food from food trucks, and participate in various children’s activities. Another notable art event is the Gold Coast Art Fair, also on June 7-8, which features thousands of art pieces from more than 200 juried artists along South Lake Shore Drive and East Monroe Street. This fair includes painting classes, a kids’ art zone, and other interactive activities.

      Sports fans have plenty to look forward to as well. The Sox Crawl: Taste of the Sox on June 7 allows you to explore Guaranteed Rate Field, the home of the Chicago White Sox, with food and drink specials, music, and autograph signings with former players like Jack McDowell.

      Outdoor adventures are plentiful in Chicago. Take a 1.5-hour guided architecture cruise on the Chicago River to explore the city's iconic skyline and learn about its architectural history. For a panoramic view of the city, visit the SkyDeck at the Willis Tower, which features a glass-floored ledge and interactive displays. Millennium Park is another must-visit, with its serene gardens, interactive fountains, and iconic sculptures like Cloud Gate.

      Food experiences are a highlight of any trip to Chicago. The Chicago Taco and Tequila Fest on June 27-28 is a great place to sample local tacos and tequilas. If you prefer barbecue, Ribfest in North Center, happening over three days, offers more than 20 food vendors, whiskey tastings, and live music.

      Cultural spots abound in Chicago. The Art Institute of Chicago is one of the top attractions, featuring a vast collection of art including works by Monet and Van Gogh, as well as the famous miniature rooms. The Museum of Science and Industry is another gem, with exhibits on a German U-Boat, the human body, and climate change, making it engaging for all ages.

      For a unique experience, consider the Chicago Mob and Crime Bus Tour, which delves into the city's history of organized crime. Alternatively, the Small-Group Night Tour with Skydeck and Skyline Cruise offers a combination of city views and a cruise along the Chicago River, providing a different perspective on the city's landmarks.

      Finally, no visit to Chicago would be complete without experiencing some of its famous festivals. The 55th annual Chicago Pride Parade on June 29 is a significant event that celebrates diversity and inclusivity, making it a vibrant and memorable experience.

      Whether you're interested in music, sports, art, outdoor adventures, cultural spots, or food experiences, Chicago has something for everyone, making it a city that is always ready to entertain and inspire.
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      4 min
    • "Exploring Chicago's Vibrant Culture, Arts, and Entertainment Offerings"

      "Exploring Chicago's Vibrant Culture, Arts, and Entertainment Offerings"
      Jun 14 2025
      Chicago, a city known for its vibrant culture, rich history, and diverse entertainment options, offers a plethora of activities that cater to all interests. Whether you are a music enthusiast, an art lover, a sports fan, or someone who enjoys outdoor adventures and unique cultural experiences, Chicago has something for everyone.

      For music lovers, the Millennium Park Music Series is a must-attend, featuring free outdoor concerts with top local and touring acts set against the stunning backdrop of the city skyline. This series runs throughout the summer, providing numerous opportunities to enjoy live music in a beautiful setting.

      If you are in Chicago this week, consider attending the Sox Crawl: Taste of the Sox on June 7 at Guaranteed Rate Field. This event allows you to explore the White Sox stadium, enjoy food and drink specials, listen to music, and even get autographs from notable players like Jack McDowell, the 1993 AL Cy Young Award winner.

      Art enthusiasts will delight in the 57th Street Art Fair, taking place on June 7-8 in Hyde Park. This 78th annual fair brings together over 150 artists to showcase their work, making it an ideal event for both seasoned collectors and newcomers to the art scene.

      For a unique cultural experience, visit the Maxwell Street Market on select Sundays. This century-old market offers a blend of unique crafts, live music, and delicious global street food, giving you a taste of Chicago's diverse cultural heritage.

      Outdoor adventures abound in Chicago, with the Chicago SummerDance being a highlight. This free event features dance lessons and live music on an open-air dance floor, allowing you to dance the night away under the stars. Additionally, the Lincoln Park Greek Fest, happening later in the summer, offers authentic Greek cuisine, music, and dancing, making it a lively and festive experience.

      Food enthusiasts should not miss the Chicago Taco and Tequila Fest on June 27-28, where you can sample top local taco spots and pair your eats with tequila. Another culinary delight is the Taste of Randolph, celebrating the best of the West Loop’s restaurant scene with gourmet bites and live music.

      Sports fans can catch a game at Wrigley Field or Guaranteed Rate Field, home to the Chicago Cubs and White Sox, respectively. For a more unique sports-related experience, the Craft Brews at Lincoln Park Zoo event allows you to sample craft beers while exploring the historic zoo, making for a fun and adults-only evening.

      Chicago's museums are also a treasure trove of interesting and unique experiences. The Art Institute of Chicago is currently hosting the exhibit "Frida Kahlo’s Month in Paris" until July 13, 2025, offering a deep dive into the artist's life and work. The Field Museum's "Africa Fashion" exhibit, which opened on February 28, 2025, is another must-see, showcasing the rich and diverse fashion traditions of Africa.

      For a blend of art and music, "Tuesdays on the Terrace" at the Museum of Contemporary Art features free live music by artists from Chicago’s internationally renowned jazz community. The "Jazzin’ at the Shedd" series at the Shedd Aquarium combines top jazz ensembles with cocktails and unbeatable skyline views, making for a sophisticated and enjoyable evening.

      To explore Chicago's iconic landmarks, consider taking the Chicago: Hop-on Hop-off Sightseeing Tour by Open-top Bus or the Chicago: 45-Minute Family-Friendly Architecture River Cruise. These tours provide a comprehensive view of the city's architectural marvels and historical sites.

      In the evenings, head to Navy Pier and enjoy a ride on the Centennial Wheel, offering panoramic views of the city skyline. For a more historical and intriguing experience, take the Chicago: Mob and Crime Bus Tour, which delves into the city's notorious past.

      Whether you are interested in music, sports, art, outdoor adventures, or cultural and food experiences, Chicago has a wealth of activities that promise to make your visit memorable and enjoyable.
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      4 min
    • Explore Chicago's Vibrant Culture, Architecture, and Entertainment in this Podcast Episode

      Explore Chicago's Vibrant Culture, Architecture, and Entertainment in this Podcast Episode
      Jun 7 2025
      Chicago, a city renowned for its vibrant culture, stunning architecture, and diverse entertainment options, offers a plethora of activities that cater to all interests. For tourists and locals alike, here are some fun, entertaining, and unique things to do in this dynamic city.

      To start your Chicago adventure, consider taking a guided architecture cruise on the Chicago River. You can choose from a 1.5-hour guided architecture cruise or a 45-minute family-friendly version, both of which provide a unique perspective on the city's iconic skyline and architectural landmarks[1][4].

      For outdoor enthusiasts, June is an excellent time to kayak down the Chicago River or rent an electric boat from the Chicago Electric Boat Company. These activities allow you to explore the city's waterways and admire its high-rise architecture from a different angle. Urban Kayaks has reopened its Riverwalk and Lakefront locations, making kayaking a magical and unforgettable experience[4].

      Music lovers have several exciting options in June. The Candlelight Concert series is a must-attend, with events like "Candlelight: Best of Bridgerton on Strings," where talented musicians perform favorite melodies from the hit series. Additionally, the Millennium Park Music Series offers free outdoor concerts featuring top local and touring acts, set against the stunning backdrop of the city skyline[4][5].

      Art and culture are deeply ingrained in Chicago's fabric. The Joffrey Ballet's production of "Alice’s Adventures in Wonderland," choreographed by two-time Tony Award-winning choreographer Christopher Wheeldon, is a family-friendly and enchanting experience that concludes the ballet's 69th season. For art enthusiasts, Uptown Art Week is a highlight, featuring over 150 public art installations and live art events[4][5].

      When it comes to popular attractions, no visit to Chicago is complete without a trip to Millennium Park. Here, you can snap a selfie with the iconic Cloud Gate sculpture (known as "The Bean") and enjoy the serene gardens and interactive fountains. The 360 Chicago Observation Deck and the SkyDeck offer panoramic views of the city, while the Museum of Contemporary Art and the Art Institute of Chicago provide extensive collections of art from around the world[3].

      Foodies will delight in Chicago's diverse culinary scene. The Taste of Randolph festival celebrates the best of the West Loop’s restaurant scene with gourmet bites and live music. For a unique dining experience, visit the historic Maxwell Street Market on select Sundays for global street food and live music. Craft Brews at Lincoln Park Zoo is another standout event, where you can sample craft beers while exploring the zoo[5].

      Sports fans can catch a game at Wrigley Field, home of the Chicago Cubs, or Guaranteed Rate Field, where the Chicago White Sox play. Even if you're not attending a game, taking a tour of these historic stadiums is a great way to experience Chicago's sports culture.

      For cultural experiences, the Lincoln Park Greek Fest is a lively street festival that celebrates the city’s Greek heritage with authentic cuisine, music, and dancing. The Jazzin’ at the Shedd series at the Shedd Aquarium features top jazz ensembles, cocktails, and unbeatable skyline views, making for a sophisticated and enjoyable evening[5].

      Finally, for those looking for hidden gems, Tuesdays on the Terrace at the Museum of Contemporary Art offers free live music from Chicago’s internationally renowned jazz community. This is a great way to experience local talent in a unique setting.

      Whether you're interested in architecture, music, art, outdoor adventures, or culinary delights, Chicago has something for everyone, making it a city that is both entertaining and enriching to visit.
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      4 min

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